Looking for some advice here. So I have done outreach before with Companies who have had major products or services that pretty newsworthy. However, how do to you outreach for smaller companies or services that do not have much of a reach.

For example, I have some sites I'm working on right now in a tight niche - video games. They have a great service (they coach players in competitive games), but getting contextual links have been pretty difficult for them as the creators of the website do not have a lot of clout in the community (however, some of the coaches do).

I'm trying to gun for big sites like Polygon, IGN, etc. I have gotten links a lot of niche forums and sites, which have been great for them, but I really want to get the big brand builders for them. Their blog and guest posts are amazing (their posts are usually over 2,000 words)

I've always done outreach through contributors before and it works for most niches, I'm just not sure if it works for this one.

A note of encouragement: It seems like the first one is the hardest to knock down. As soon as you have one published it's a lot easier to use the bandwagon approach to get the other sites to follow suit.

Do you know anybody that works at those sites you reference? That's the best way in my experience - find out who writes and just make the direct appeal. There are numerous services which can provide emails of media and they're worth the investment.

I would suggest connecting on LinkedIn or Twitter and build a relationship up. Comment on their posts, share their links, etc. While it takes time, by building that relationship, you have a better chance of getting authors/journalists of larger sites to reciprocate. They're at least much more likely to pay attention to your email that comes through when you ask for the favor as it won't be so 'cold'.

When we were providing our clients with subscriptions with Vocus (the more corporate version of PRWeb), the company was bought out by another company called Cision.

Cision provided press releases too, but they also provided a media outreach service which looked very interesting.

If I had clients with deeper pockets, I'm sure that type of program would have worked for them. The service put you in touch with opt-in media managers and movers in your particular industry. And the idea is the mechanism of the service puts you in touch with the right people for media mentions in magazines, news papers and blogs along with some other buzz-worthy targets. But that particular service had nothing to do with links.

I really like that idea of "media outreach", but never really fully tested the potential.

I agree with the above points, however, I'd like to add this:
Since these sites have +2000 word articles as you said, think about their design, is it professional, it looks good and well built? That has a big impact on those who may think about your email and when they visit the site, the design kills everything.

Also, have you tried HARO? (help a reporter), it's great but for those who have the expertise, so here is what you can do, signup and receive emails about journalists looking for gaming experts or so, then, forward the questions asked by the journalist to the website owner, then, send back the email with one paragraph or so and add his site link. That worked for many and got mentions from big sites like The NewYork Times and others but it need time and patience. I hope that this can help.

I agree with the above points, however, I'd like to add this:
Since these sites have +2000 word articles as you said, think about their design, is it professional, it looks good and well built? That has a big impact on those who may think about your email and when they visit the site, the design kills everything.

Also, have you tried HARO? (help a reporter), it's great but for those who have the expertise, so here is what you can do, signup and receive emails about journalists looking for gaming experts or so, then, forward the questions asked by the journalist to the website owner, then, send back the email with one paragraph or so and add his site link. That worked for many and got mentions from big sites like The NewYork Times and others but it need time and patience. I hope that this can help.

Yes, I have tried HARO. Is it rarely helpful for me because the stuff I write for is very nichy. I haven't tried video games though so let me update my profile and see what happens.